Install Exchange Server 2019

I’ve set up Exchange Server 2019 a few times now—mostly for mid-sized clients who still prefer on-prem mail over cloud. Not gonna lie, the first time I tackled this, I underestimated how picky Exchange can be about its environment. If you’re planning to deploy it, especially on Server 2019, here’s how I approached it, what tripped me up, and what I’d do differently next time.

Why I Went with Exchange 2019

One client had aging Exchange 2013 boxes and wanted something more stable without jumping to the cloud. Exchange 2019 felt like the right balance—modern enough to support SSD optimization and better search indexing, but still familiar. Plus, they had the licensing already sorted via Volume Licensing, so it made sense.

Setup Walkthrough (With Commentary)

Here’s how I got it running on a Hyper-V VM with 32GB RAM, Windows Server 2019 Standard, and a clean AD environment:

• Prep the Environment
  Joined the VM to the domain, made sure the account had Enterprise Admin and Schema Admin rights (since this was the first Exchange box). Installed the required Windows features using PowerShell—don’t skip this, or the setup will fail halfway through.
• Mount the ISO & Launch Setup
  Mounted the Exchange 2019 ISO and ran Setup.exe as admin. The wizard is straightforward, but I always choose to skip updates during install and patch later—less chance of mid-install surprises.
• Role Selection
  I went with the Mailbox role only. Most guides suggest separating roles, but for smaller environments, consolidating roles works fine. Management tools get installed with it anyway.
• Readiness Checks
  This part can be deceiving. The wizard might say “ready,” but I’ve had installs fail later due to missing .NET versions or lingering prerequisites. I now double-check manually before clicking “Install.”
• Installation
  Took about 40 minutes. The screen just sat there—black, silent, almost mocking me. No progress bar, just logs updating in the background. If you’re impatient, keep Task Manager open to reassure yourself it’s doing something.
• Post-Install
  Once done, I launched Exchange Admin Center (EAC) via browser. It loaded fine, but I had to tweak virtual directories and set up the default database manually. Also, don’t forget to configure mail flow connectors—Exchange won’t do that for you.

Gotchas & Bugs I Hit

• Server Renaming
  One rookie mistake I made early on: renamed the server after install. Exchange doesn’t like that. Broke services, had to reinstall from scratch. Lesson learned—name your server properly before setup.
• TLS Issues
  On one install, Outlook clients couldn’t connect. Turned out to be a TLS mismatch. Had to manually enable TLS 1.2 in the registry and reboot. Most guides skip this, but it’s crucial if you’re running newer clients.
• Schema Prep Confusion
  If you’re installing in an existing AD forest, make sure schema prep is done. I used Setup.exe /PrepareSchema and Setup.exe /PrepareAD manually before the GUI install. Saves you from permission errors later.

What I’d Do Differently

• Use PowerShell for most post-install config. The GUI is fine, but scripting saves time and ensures consistency.
• Snapshot the VM before install. If something goes sideways, you’ll thank yourself.
• Document everything—especially connector settings and accepted domains. Exchange doesn’t always make it obvious what’s missing.

Final Thoughts

Exchange 2019 isn’t plug-and-play, but once it’s up, it’s solid. Just be methodical. Don’t rush the prep, and don’t assume the wizard will catch everything. If you’ve got a clean AD and follow the prerequisites to the letter, the install itself is uneventful.

Ever had Exchange throw a cryptic error mid-install? Or spent an hour debugging a typo in a connector name? Drop your war stories below—I’d love to hear how others are handling their Exchange setups.